Outlook’s Autodiscover Redirect Limit – Hybrid Autodiscover Breaking for Exchange Online Mailboxes / Remote On-Premises Mailboxes

Scenario:  After introducing additional Exchange On-Premises servers, we noticed that Autodiscover stopped working for our Exchange Online Hybrid mailboxes that were on computers internal to the domain. Using the ‘Test E-mail AutoConfiguration’ feature in Outlook, it would fail after the SCP/DNS autodiscover lookup.

Reason:  Outlook has an Autodiscover Redirect limit of 8-10 responses.  Being we had more than 10 servers in our Exchange Infrastructure, once it hit the response limit from each SCP lookup for each server, it would then fail all redirects thereafter. You do not need 100 SCP Failures if its going to fail after the first 10 servers.

Solution:  You can reduce the number of SCP lookup’s by performing any of the following.

  1. Set the AutoDiscoverSiteScope value on each Exchange server so it only serves requests for each  AD Site via the following command:  Set-ClientAccessServer ExSrv1 -autodiscoversitescope NewYork   (Or a combination NewYork,Baltimore,Tampa)
  2. Set the AutoDiscoverSiteScope to $null so it does not participate in SCP lookups via the following command: Set-ClientAccessServer ExSrv1 -AutodiscoverSiteScope $null
  3. Set the AutoDiscoverServiceInternalURI to $null so it does not participate in SCP lookups via the following command: Set-ClientAccessServer ExSrv1 -AutodiscoverServiceInternalURI $null



Emails in users “Inbox” are automatically moved to a folder (not created by user), labeled “Junk”


A new email arrives, it sits in the “Inbox” anywhere from a few seconds to a few minutes before it moves to a folder labeled “Junk”. This is not the default “Junk E-Mail” folder in Outlook/OWA.


Client has a Samsung Galaxy device configured to view users mailbox.


  1. Go into the E-Mail application on the Samsung Galaxy
  2. Press the Menu Key, select Settings, then General Settings
  3. Select Spam addresses and remove any addresses that should not be in there, such as your corporate domain.

Export or manually archive Outlook 2011 for MAC items

An easy way to reduce the size of your Inbox is to export — manually archive to an ‘Outlook for Mac Data File’ (.olm) on your Mac — your e-mail messages, contacts, and other items. You can still access this data at any time, and you can even transfer individual items, or the entire Data File, to Outlook for Mac on another computer.

NOTE   In Outlook for Windows, older Outlook items are archived automatically on a regular interval, also known as Auto Archive. This is not available in Outlook for Mac, but you can archive data automatically by setting up Time Machine.

Do any of the following:

Export to an Outlook for Mac Data File
When you export to an Outlook for Mac Data File, you can choose to filter information by category or by item type. For example, if you want to transfer networking information from your work computer to your home computer, you could export only items that you’ve assigned to the Networking category. Similarly, you might want to export all your contacts on your home computer and then import them on your work computer. During the export process, you can choose to keep the exported items in Outlook, or to delete them after they are exported.
1. On the File menu, click Export.
2. Click Outlook for Mac Data File.
3. Select an option to filter by category or item type. To export all items in Outlook, click Items of the following types, and then select all the check boxes.
4. Click the right arrow to continue, and then follow the instructions. The Outlook for Mac Data File uses the .olm extension.

– If you have a Microsoft Exchange account or directory services account, contacts from the directory are not exported. Similarly, items that are stored in public folders are not exported.
– An Outlook for Mac Data File does not contain account settings or your Outlook preferences.

Export contacts in a tab-delimited text file
To transfer a set of contacts to another computer or application, you can export contacts as a tab-delimited text file, which can be opened by many other mail, spreadsheet, and database applications.
1. On the File menu, click Export.
2. In the Export Assistant, click Contacts to a list, and then follow the instructions. Tab-delimited files are saved with a .txt extension.

– If you have a Microsoft Exchange account or directory services account, contacts from the directory are not exported.
– When you export a contact, all the information in Outlook that is related to that contact — such as mailing addresses, birthday, and notes — is included. However, some mail applications might be unable to display the contents of certain fields such as “Spouse/Partner” and “Interests.”
– Encryption certificates aren’t exported.

Export individual items
You can also export single items as individual files, either to have as a backup or to use in other applications.
1. In the item list, select the item that you want to export. To select multiple items, hold down   as you click the items.
2. Drag the selection to the desktop or a folder in the Finder.

– E-mail messages are exported as .eml files.
– Contacts are exported as vCard (.vcf) files.
– Calendar events and tasks are exported as .ics files.
– Notes are exported as .html files.

Outlook 2011 for MAC not receiving mail

Scenario: “I’m not receiving e-mail or other items in my Exchange account” for Outlook for Mac.
Cause1: Outlook is offline.
Solution1:    Verify that Outlook is online. On the Outlook menu, make sure that Work Offline is not checked. 

Cause2: Outlook is not connected to the server that is running Microsoft Exchange Server.
Solution2:    Check your Microsoft Exchange server connection.  On the Tools menu, click Accounts. Look at the Exchange account in the left pane. If there is a problem with the connection, the indicator icon will be orange.
If you successfully connected to the account before, try to connect to it from another Exchange application, such as Outlook Web App.

Cause3: Items from an Exchange account are stored in the Outlook cache. If this cache becomes corrupted, it may cause synchronization problems with the Exchange server.

Solution3:    Empty the cache in Outlook so that Outlook can download all the items from your Microsoft Exchange account again.

CAUTION   The following procedure deletes any information that is not synchronized with the Exchange server, including your contacts’ mail certificate. Before emptying the cache, you may want to back up your Outlook information that is stored only locally on your computer. Make sure that your computer is connected to the Exchange server.

1.     In the navigation pane, press CONTROL and click the Exchange folder for which you want to empty the cache, and then click Folder Properties.

2.     On the General tab, under Empty Cache, click Empty.
After the folder is empty, Outlook automatically downloads the items from the Exchange server.

Manually downloading a copy of the Offline Address Book.

Scenario: You expect to see a user in the Offline Address Book, but you cannot find that user. The Offline Address Book is used when Outlook is in Cached mode.

Solutions:  Outlook is supposed to download the offline address book every 24 hours. Additions/Modifications made to users in the address book may not be seen by someone who is using an older version of the offline address book. We have seen a restart of the computer force Outlook to download it if Outlook has not updated for a while, but you can attempt to manually download a new copy of the Offline Address Book.

Outlook 2010/2013 

1. Click the Send/Receive Tab, click Send/Receive Groups, Select Download Address book.
2. Uncheck the box next to Download changes since last Send/Receive. In the Information to download section, select Full Details and in the Address Book section, choose Global Address List. click OK.
3. The offline address book will start to download. A status window will open to indicate that the download is in progress and will close automatically when the download is complete.

Outlook 2007 

1. Click on Tools, highlight Send/Receive, select Download Address Book.
2. Uncheck the box next to Download changes since last Send/Receive. In the Information to download section, select Full Details and in the Address Book section, choose Global Address List. Click OK.
3. The offline address book will start to download. A status window will open to indicate that the download is in progress and will close automatically when the download is complete.

Outlook 2011 on OSX

1.Fully exit Outlook 2011
2.Remove the ~/Library/Caches/Outlook/Main Identity directory
3.Restart Outlook 2011

If the user is not in the offline address book, verify you can find the user via Outlook Web App. 

Configuring a new identity for Outlook 2011

Scenario:  You wish to create a new identity for Outlook 2011 and re-configure Outlook 2011 with your exchange mailbox.

1. Open the Microsoft Database Utility. The default location is in /Applications/Microsoft Office 2011/Office/.  Tip: You can also open the Database Utility if you close Outlook, hold down the OPTION key, and then click the Outlook icon in the Dock.

2. Do one of the following:
   1. Create a new identity:  Click Add via the + button and type a name for the new identity.
   2. Rename an identity: Double-click the identity, and then type a new name for the identity.
   3. Delete an identity: Click the identity you wish to remove and click delete via the – button.

3. Switch the identity:
   1. Click on the identity you wish to become active.
   2. Click the gear button and choose ‘Set as Default‘.

4. Open Outlook:
   1. If this is the first time you’ve opened Outlook 2011, you will be automatically prompted to add an account. If you have an account configured already, click on Tools –> Accounts from the menu bar. Click the + and add an Exchange… account.
   2. In the Welcome to Outlook for Mac window, check Make Outlook the default application for e-mail, calendar, and contacts.  Click on Add Account.
   3. In the Add an Account window, click on Exchange Account.
   4. In the Enter your Exchange account information, enter the following and click Add Account.
        a. E-Mail Address
        b. Select User Name and Password for the Method.
        c. User name *include Domain in front of the user name.
        d. Password
        e. Check configure automatically.

5. Exit out of the Accounts window.

Outlook 2011 is now configured and your email will start downloading momentarily.

EWS is giving HTTP Status 500’s for specific users

Scenario:  You have a user complaining that they cannot access mail through Outlook 2011. When you search the Exchange servers IIS logs, you see a bunch of HTTP 500 responses provided by the Exchange server only for that user.  You also found out that this user is on travel.

Resolution:  Instead of changing the timezone to reflect the area the user was in, the user adjusted the current time.  Changing the timezone to where they were at or adjusting the time back to the current time of the original time zone resolved this issue.

Subscribing to folders in Outlook 2011 when using IMAP

Scenario: When you are using Outlook 2011 and your mail profile is setup to connect via IMAP, you may not see all of your folderssubfolders in your mailbox.
Solution: These folders may need to be subscribed to. Follow these steps to import these folders into Outlook 2011.
1. With Outlook 2011 open, select Tools –> IMAP Folders.
2. You will see a list of folders available to import into Outlook. You can click each folder and select Subscribe.
3. The new susbscribed folders will now be located in the folder list on the left hand pane of Outlook.

Out of Office Not Working for a Single User

Issue: Out of Office is turned on for a user, but a Out of Office notification is not beingsent to internal/external users. You may see the Out of Office message internally BEFORE you send the message in the Outlook notification bar in the new message window.

Cause: Mailbox rules have corrupted or are conflicting with the Out-Of-Office rule in order to send a message to recipients.
Resolution: The resolution is to remove the conflicting rules in the mailbox. To do this:
1. From a run prompt use the following switch: outlook.exe /cleanrules .This will clean client and server rules for the mailbox. This is the fastest way of fixing this issue.
2. You can manually remove each rule in the mailbox.